Hydrochloric Acid → 4'-[(4-{4-[1-(1-Acetylcyclobutyl)ethoxy]cyclohexyl}-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)methyl]biphenyl-2-carbonitrile

HRID 519795노트

반응식

HRID 519795 반응식
[CH:1]([C:3]1([CH:7]([O:9][CH:10]2[CH2:15][CH2:14][CH:13]([N:16]3[C:21](=[O:22])[C:20]([CH2:23][C:24]4[CH:29]=[CH:28][C:27]([C:30]5[C:31]([C:36]#[N:37])=[CH:32][CH:33]=[CH:34][CH:35]=5)=[CH:26][CH:25]=4)=[C:19]([CH2:38][CH2:39][CH3:40])[N:18]4[N:41]=[CH:42][N:43]=[C:17]34)[CH2:12][CH2:11]2)[CH3:8])[CH2:6][CH2:5][CH2:4]1)=[O:2].[CH3:44][Mg]Br.O1CCCC1.Cl>O1CCCC1>[C:1]([C:3]1([CH:7]([O:9][CH:10]2[CH2:15][CH2:14][CH:13]([N:16]3[C:21](=[O:22])[C:20]([CH2:23][C:24]4[CH:25]=[CH:26][C:27]([C:30]5[C:31]([C:36]#[N:37])=[CH:32][CH:33]=[CH:34][CH:35]=5)=[CH:28][CH:29]=4)=[C:19]([CH2:38][CH2:39][CH3:40])[N:18]4[N:41]=[CH:42][N:43]=[C:17]34)[CH2:12][CH2:11]2)[CH3:8])[CH2:6][CH2:5][CH2:4]1)(=[O:2])[CH3:44]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 866440584'-[(4-{4-[1-(1-Formylcyclobutyl)ethoxy]cyclohexyl}-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)methyl]biphenyl-2-carbonitrileHCID 178420675HCID 178420675, 화합물

생성물 1

HCID 670091324'-[(4-{4-[1-(1-Acetylcyclobutyl)ethoxy]cyclohexyl}-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)methyl]biphenyl-2-carbonitrile

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 4′-[(4-{4-[1-(1-formylcyclobutyl)ethoxy]cyclohexyl}-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)methyl]biphenyl-2-carbonitrile (10.35 g) in tetrahydrofuran (50 mL) was added 1 M methylmagnesium bromide-tetrahydrofuran solution (27 mL), and the mixture was stirred at room temperature for 15 hr. 1 N Hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. To a solution of the residue in acetonitrile (200 mL) was added 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one (8.48 g), and the mixture was stirred at room temperature for 2 hr. Saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography [eluent: hexane/ethyl acetate=80/20→60/40 (volume ratio)] to give the title compound as a colorless amorphous compound (8.32 g, 79%).

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. additionTo a solution of the residue in acetonitrile (200 mL) was added 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one (8.48 g)
  6. stirringthe mixture was stirred at room temperature for 2 hr
  7. additionSaturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture
  8. extractionthe mixture was extracted with ethyl acetate
  9. washThe extract was washed with saturated brine
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customThe solvent was evaporated under reduced pressure
  12. customthe residue was purified by silica gel chromatography [eluent: hexane/ethyl acetate=80/20→60/40 (volume ratio)]

출처 및 근거

ORD 기록
ord-7db99a61b12c42c1a527509377d0271e
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09115136B2

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